CN114605298B - Fluorine-containing benzoyl thiourea insecticide and acaricide - Google Patents
Fluorine-containing benzoyl thiourea insecticide and acaricide Download PDFInfo
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- CN114605298B CN114605298B CN202210397937.1A CN202210397937A CN114605298B CN 114605298 B CN114605298 B CN 114605298B CN 202210397937 A CN202210397937 A CN 202210397937A CN 114605298 B CN114605298 B CN 114605298B
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- acaricide
- containing benzoyl
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- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 16
- 239000000642 acaricide Substances 0.000 title claims abstract description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 8
- 239000011737 fluorine Substances 0.000 title claims abstract description 8
- 239000002917 insecticide Substances 0.000 title abstract description 4
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 241000238876 Acari Species 0.000 claims abstract description 13
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 11
- -1 benzoyl thiourea compound Chemical class 0.000 claims abstract description 8
- 230000000749 insecticidal effect Effects 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000002147 killing effect Effects 0.000 abstract description 13
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 241000500437 Plutella xylostella Species 0.000 description 11
- 239000000575 pesticide Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QVAUOEHPYOFAQA-UHFFFAOYSA-N 4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylaniline Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1N QVAUOEHPYOFAQA-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 239000005912 Lufenuron Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 3
- 229960000521 lufenuron Drugs 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940125890 compound Ia Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 description 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 description 1
- YPSCQJTUAKNUNF-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl YPSCQJTUAKNUNF-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- YYXSCUSVVALMNW-FOWTUZBSSA-N pyriminostrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 YYXSCUSVVALMNW-FOWTUZBSSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
- C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Abstract
The invention provides a fluorine-containing benzoyl thiourea compound, which has a structure shown in a general formula I:wherein R is:
Description
The invention belongs to the field of pesticides and acaricides in pesticides, and relates to a fluorine-containing benzoyl thiourea pesticide and acaricide for controlling pest mites in agriculture or forestry.
Background art agricultural pests and mites harm the growth of crops, resulting in reduced yield and reduced quality. At present, the control of pest mites mainly depends on chemical pesticides, and because a large number of frequently used pesticides and acaricides are adopted, the pest mites have serious drug resistance to the chemical pesticides, so that the dosage is larger and larger, the control effect is lower and lower, the duration is shortened, the pesticide residue is increased and the like. The development and application of novel insecticidal and acaricidal agents with different action mechanisms are effective means for solving the problem of pest resistance. The fluorobenzoyl thiourea compound has insecticidal activity, and commercial benzoyl thiourea pesticides mainly comprise: diflubenzuron, chlorbenzuron, lufenuron, flufenoxuron and the like.
The compounds of the present invention have some structural similarities with the fluorobenzoyl thiourea compounds described above, but the compounds of the general formula I and their use as agricultural insecticidal acaricides as described in the prior art are not disclosed.
The invention aims to provide an insecticidal and acaricidal agent which has novel structure, simple and convenient synthesis method, safety and high efficiency and can be used for preventing and controlling agricultural or forestry pest mites.
The technical scheme of the invention is as follows:
a fluorine-containing benzoyl thiourea compound has a structure shown in a general formula I:
wherein R is:
the compounds of the general formula I according to the invention can be prepared by the following processes:
wherein R is as defined above. The specific preparation method is shown in the synthetic example of the invention. Table 1 shows the structure and appearance of the compounds of formula I.
TABLE 1 Structure and appearance of Compounds of general formula I
The invention has the advantages and positive effects that:
the compound (formula I) of the invention is used as agricultural insecticide and acaricide, and has the advantages of novel structure, simple and convenient preparation and insect and mite treatment. The compound has good inhibiting and killing effects on plutella xylostella and tetranychus cinnabarinus, and can achieve the excellent effect of simultaneously controlling insect pest mites of agriculture and forestry. Especially, ib and ic have excellent killing effect on plutella xylostella, the killing rate reaches 94% and 100% respectively at a low concentration of 5mg/L, and ic exceeds commercial lufenuron. The compound has an inhibiting and killing effect on tetranychus cinnabarinus, wherein the inhibiting and killing effect on Ib and Ic is good, and the concentration of the compound reaches more than 90 percent at 50 mg/L. The compound is a fluorine-containing ureide compound, has the characteristics of high biological activity, low toxicity to beneficial organisms, easy degradation and good environmental compatibility, is particularly suitable for the treatment of pesticide-resistant agricultural pest mites commonly existing at present, and has good development and application prospects as a novel variety of pesticides with the functions of killing insects and mites.
The compound can be used independently or in combination with other active substances to improve the comprehensive performance of the product.
The invention also comprises an insecticidal and acaricidal composition taking the compound shown in the general formula I as an active component, wherein the weight percentage of the active component in the composition is 1-99%. The insecticidal and acaricidal composition also comprises an agriculturally or forestry acceptable carrier.
It should be understood that various changes and modifications can be made within the scope of the present invention as defined in the appended claims.
Detailed Description
The following synthetic examples, green test results, are useful for further illustration of the invention and are not meant to limit the invention.
Synthesis example
Example 1 preparation of Compound Ia:
(1) Synthesis of 2, 6-difluorobenzoyl chloride:
into a 250mL single-necked flask, 80mL of toluene and 15.8g (0.1 mol) of 2, 6-difluorobenzoic acid were charged, 17.7g (0.15 mol) of thionyl chloride was further added, three drops of DMF were added dropwise, and a condenser was connected to a dryer and an alkali absorption device to absorb acid gas. Stirring, heating and refluxing for 2h, allowing the liquid in the bottle to be light yellow transparent, cooling to room temperature after TLC monitoring reaction completion, decompressing and removing solvent toluene and unreacted complete thionyl chloride to obtain yellow brown viscous liquid, diluting and cleaning the flask with 20g of 1, 2-dichloroethane to obtain 36.7g of acyl chloride mother liquor with 45.5% content, and sealing for later use.
(2) Synthesis of 2, 6-difluorobenzoyl thioisocyanate:
20g of 1, 2-dichloroethane is placed in a 100mL three-neck flask equipped with a mechanical stirring device, 1.94g (0.02 mol) of dry potassium thiocyanate solid is weighed and added into the flask, one drop of polyethylene glycol-200 is added as a catalyst, 3.91g (0.01 mol) of acyl chloride mother liquor of the last step is slowly added into the flask by a constant pressure dropping funnel for stirring at room temperature, the reaction is carried out for 2 hours, TLC monitoring (developing agent V (petroleum ether): V (ethyl acetate) =7:1) is carried out, and the reaction bottle is sealed after the reaction is completed, and the next reaction is carried out without treatment.
(3) Synthesis of Compound Ia:
2.61g (0.095 mol) of 2-methyl-4- (perfluoropropan-2-yl) aniline and 5g of 1, 2-dichloroethane are taken and mixed well in a 10mL beaker and transferred to a constant pressure dropping funnel. Heating the solution in the three-neck flask of the reaction in the previous step to 80 ℃, slowly dropwise adding 2-methyl-4- (perfluoropropane-2-yl) aniline mother liquor, continuously heating to reflux after the dropwise adding is finished, reacting for 0.5h, monitoring (developing agent V (petroleum ether): V (ethyl acetate) =7:1) by TLC, after the 2-methyl-4- (perfluoropropane-2-yl) aniline is completely reacted, cooling to room temperature, adding 20mL of deionized water into the reaction flask, stirring for 5min, transferring to a separating funnel, adding a proper amount of 1, 2-dichloroethane for extraction, washing twice with saturated saline, drying an organic phase with anhydrous sodium sulfate, and removing a solvent to obtain dark brown oily liquid. The white solid is obtained by column chromatography and purification, and the yield is 85.1%.
Compounds Ib, ic, id are prepared in a similar manner.
The nuclear magnetic data of the compounds of the general formula I of the invention are as follows:
compound la: 1 H NMR(500MHz,DMSO-d 6 )δ12.36(s,1H),11.94(s,1H),7.91(d,J＝8.7Hz,1H),7.65–7.60(m,2H),7.55(s,1H),7.27(d,J＝8.4Hz,1H),7.24(s,1H),2.36(s,3H).
compound ib: 1 H NMR(500MHz,DMSO-d 6 )δ12.41(s,1H),11.68(s,1H),7.78(d,J＝2.2Hz,1H),7.66(d,J＝2.1Hz,1H),7.63(dd,J＝8.5,6.5Hz,1H),7.26(t,J＝8.2Hz,2H),2.39(s,3H).
compound ic: 1 H NMR(500MHz,DMSO-d 6 )δ12.07(s,1H),10.82(t,J＝5.7Hz,1H),7.65–7.55(m,1H),7.43–7.38(m,2H),7.22(d,J＝8.3Hz,2H),7.20–7.16(m,2H),6.99–6.94(m,2H),6.94–6.89(m,2H),4.83(d,J＝5.7Hz,2H),2.28(s,3H).
compound id: 1 H NMR(400MHz,Chloroform-d)δ10.62(s,1H),9.06(s,1H),7.49(ddd,J＝8.5,6.3,2.2Hz,1H),7.42–7.39(m,2H),7.35–7.31(m,2H),7.02(t,J＝8.4Hz,2H),4.85(d,J＝5.2Hz,2H),1.33(s,9H).
biological Activity test
Example 2 insecticidal Activity assay
(1) Method for measuring activity of killing plutella xylostella
The specific implementation method is as follows: the sample to be tested is a mixed solution of a compound with a certain concentration and DMF, and then is diluted into liquid medicine with different concentration gradients by using 0.1% Tween-80. Taking fresh and clean cabbage leaves as a plutella xylostella feeding sample, cutting the taken cabbage leaves into wafers with uniform size and shape by using a puncher with the diameter of 5cm, soaking the wafers into the prepared medicinal liquid with gradient concentration for 15-20 times, taking out the soaked wafers, setting clear water as a blank control, repeating each concentration for three times, and airing. The culture dish is padded with double-layer filter paper with the same diameter and is wetted by clean water, and the leaf blade is placed on the filter paper. And (3) placing 30 plutella xylostella larvae with the same growth state in a culture dish, controlling the temperature in the culture dish to 25 ℃, controlling the relative humidity to 60%, controlling the photoperiod to LD=16:8, and observing and recording the growth state of plutella xylostella. When the culture time of the plutella xylostella is 72 hours, the death number of the plutella xylostella larvae in the culture dish is checked and recorded (dead state check: stiff body, convulsion and the death of larvae is regarded as that the brush light touch bodies cannot independently crawl or are severely distorted). The final results of the experiments are the average of three groups of experiments for each concentration.
TABLE 2 results of Plutella xylostella killing Activity test of Compounds of general formula I
The test result shows that the compound has killing activity on plutella xylostella, especially that Ib and ic have excellent killing effect on plutella xylostella, and the killing rate reaches 94% and 100% respectively at low concentration of 5mg/L, and ic is higher than lufenuron.
Example 3 method for determining acaricidal Activity
The mite killing activity test is carried out on the compound, the test method is a spray method, the test object is tetranychus cinnabarinus, and the specific operation method is as follows:
diluting the prepared 500mg/L medicinal liquid with 0.1% Tween-80 to obtain samples with different concentrations, adding into a Potter spray tower, and setting pressure to 1.47×10 5 And (5) MPa. 30 mites are inoculated on round broad bean leaves with the diameter of 5cm, and three groups are arranged for each concentration. Then placing the leaf blade with the mite in a Potter spray tower, spraying 1mL of liquid medicine, placing in a constant temperature incubator at 25 ℃ for culturing for 48 hours after spray treatment, observing and recording the death number of the tetranychus cinnabarinus, and calculating the death rate of the mites according to a formula.
TABLE 3 acaricidal Activity test results for Compounds of the general formula I
The test result shows that the compound has a good inhibition effect on tetranychus cinnabarinus, wherein Ib and Ic have good inhibition effect, and the concentration of the compound reaches more than 90 percent at 50 mg/L. But all lower than pyriminostrobin.
Claims (3)
1. A fluorine-containing benzoyl thiourea compound has a structure shown in a general formula I:
2. the application of the fluorine-containing benzoyl thiourea compound as claimed in claim 1, wherein the compound of the general formula I is used as an agricultural or forestry insecticidal acaricide and has a control effect on agricultural pest mites.
3. An insecticidal and acaricidal composition comprising a compound of the general formula i as defined in claim 1 as active ingredient and an agriculturally or forestry acceptable carrier.
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|---|---|---|---|---|
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| US4310530A (en) * | 1979-09-07 | 1982-01-12 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl N-pyridyloxy phenyl urea |
| US4468405A (en) * | 1981-07-30 | 1984-08-28 | The Dow Chemical Company | Substituted N-aroyl N'-phenyl urea compounds |
| JPS59167557A (en) * | 1983-03-12 | 1984-09-21 | Kumiai Chem Ind Co Ltd | Benzoylurea derivative and insecticide |
| US4713396A (en) * | 1984-09-20 | 1987-12-15 | Nippon Soda Co., Ltd. | Benzoylurea derivatives |
| US4873264A (en) * | 1983-05-20 | 1989-10-10 | Rhone-Poulenc Nederlands B.V. | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation |
-
2022
- 2022-04-11 CN CN202210397937.1A patent/CN114605298B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933908A (en) * | 1970-05-15 | 1976-01-20 | U.S. Philips Corporation | Substituted benzoyl ureas |
| US4234600A (en) * | 1978-10-07 | 1980-11-18 | Bayer Aktiengesellschaft | Combating arthropods with N-benzoyl-N'-tert.-alkoxycarbonylphenyl-(thio) ureas |
| US4310530A (en) * | 1979-09-07 | 1982-01-12 | Ishihara Sangyo Kaisha Ltd. | N-benzoyl N-pyridyloxy phenyl urea |
| US4468405A (en) * | 1981-07-30 | 1984-08-28 | The Dow Chemical Company | Substituted N-aroyl N'-phenyl urea compounds |
| JPS59167557A (en) * | 1983-03-12 | 1984-09-21 | Kumiai Chem Ind Co Ltd | Benzoylurea derivative and insecticide |
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